Preparation of Cyclohexane Carboxylate Derivatives

Kent etal, US Patent 6,518,438 (February 11, 2003) Assignee Gilead Sciences, Inc. [Pg.28]

X- Sodium azide, ammonium chloride, triphenylphosphine oxide, water, acetic anhydride [Pg.28]

A solution of 1,3,4,5-tetrahydroxycyclohexanoic acid (104 mol) (quinic acid, [a]o = 43.7°) and p-toluenesulfonic acid monohydrate (1.05 mol) dissolved in acetone (80 kg) were refluxed for 2 hours, quenched with 21% sodium ethoxide (1.05 mol) in ethyl alcohol, and the solvent removed. The reside was partitioned between EtOAc/water, 108 kg/30 kg, the organic layers isolated, washed with 5% NaHC03 (14 kg), and a yellow solid isolated and used directly. [Pg.29]

The crude lactone from Step 1 (70 kg) was treated with 20% sodium ethoxide (1.05 mol) in ethyl alcohol. After 2 hours at ambient temperature, HO Ac (1.05 mol) was added, the solvent removed, and the product mixture isolated in 70% yield and used directly. [Pg.29]

l-Hydroxy-3,4-(2,2-dimetbyl-l,3-dioxolane)-5-mestyl-l-etboxycarbonyl-cyclobexane [Pg.29]

Big Chemical Encyclopedia